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Anyone who has been to Havana since the rapprochement between the United States and Cuba late last year would have seen the green shoots of optimism amidst the capital's crumbling beauty.

There's the once implausible sight of U.S. flags on the dashboards of sputtering taxis, and the scramble of American tourists in hotel lobbies, providing an economy drained of cash with thick transfusions of dollars. People here have jumped ahead of politics: Despite the decades of implacable tension, they don't speak warily of the Imperialist Menace to the north. Instead they line up outside private homes to buy pirated paquetes – thumb drives stocked up with films and television shows such as Homeland and The Walking Dead.

While politicians haggle over what seem like minor details – yet are almost insurmountable differences – the people of these two feuding political systems have been in the midst of rediscovery. The lifting of travel restrictions has led to a spike in visits. In the first seven months of this year, nearly 89,000 Americans travelled to Cuba, according to a study by the University of Havana, marking a 54 per cent increase over last year.

It may seem that Secretary of State John Kerry will have closed the historical wounds between the countries by formally reopening the U.S. Embassy in Havana on Friday. But diplomatic relations are the easy part.

"There has been far too much irrational belief in what's been happening," said John Kavulich, president of the U.S.-Cuba Trade and Economic Council . "People just aren't paying attention to facts. It's more about aspirations and dreams."

While President Obama and Democrats such as Vermont Senator Patrick Leahy have championed detente, a potential Republican president in 2017 may feel differently about warming relations. There are political difficulties in the immediate future as well, including, for example, how to engage the country on the issue of free speech.

Even more thorny is the normalization of trade. As a provocative offering for his 89th birthday this week, former Cuban president Fidel Castro repeated demands that the U.S. owes his country "numerous millions of dollars" for damages caused by its decades-long embargo.

Many U.S. politicians and companies, as well as Cuban expatriates, would argue otherwise. If the Cubans want the United States to end its crippling economic embargo, they're going to have to address an obstacle that will no doubt lose dozens of lawyers and bureaucrats in an ocean of fine print and mutual recrimination. The seizures of property during the Cuban revolution have left registered claims estimated to be worth at least $7-billion.

A two-decade-old U.S. law dictates that there will be no normalization in trade until the claims issue is settled. The $7-billion sum is not pocket change for Cuba, which has barely enough money to feed and care for its own people since the implosion of its big petro-papa, Venezuela.

The largest claim belongs to Staples Inc., which, in a recent takeover, inherited Office Max's claim for $270-million. But there are also personal claimants such as Cuban exile Javier Garcia-Bengochea, a neurosurgeon from Jacksonville, Fla., whose family's port property in Santiago was seized by the Communists when he was a toddler. His share of that land, he says, is now worth $90-million, factoring in compounded growth over the past 55 years. At some point in the near future, the U.S. government will represent him and hundreds of other claimants at the bargaining table.

There are several ways the two sides can bridge their differences over the claims: a pennies-on-the-dollar compromise, for example, or a cut of future business on transactions.

Dr. Garcia-Bengochea believes it is perilous to court a regime he says is lawless and hope an agreement would be enforceable. "We are patronizing a failed state," he said. "It's like being Tiger Woods' next girlfriend. Each one thinks she's going to be the real thing."

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